Most buyer's remorse I've had has come with the purchase of expensive gadgetry. But I've figured out something about buyer's remorse lately: I only experience it when the thing I buy isn't directly used in something I do creatively -- and necessary to achieve that level of creativity.
For example, my new camera. It was expensive. Buyer's remorse? Zero. I knew I needed to take better pictures of my family and this was what I needed to buy to do it.
Another example: Xbox 360. Buyer's remorse? Maybe a little. I barely use the thing. I like it a lot, but when I play it I feel like I'm wasting time with no upside for doing it.
Probably the items I've felt the most amount of buyer's remorse about are all Apple products I've ever bought. My Centris 650, which I spent $4500 on back in 1992. My Powerbook G3 -- $3100 in 1999. An iPod I bought and returned a few years ago. I have always ended up with that feeling of being ripped off when I've bought Apple equipment because I know I can get the same job done with a cheaper PC solution.
Maybe I'm a weirdo because I don't think MacOS X helps creativity on the computer. That's why I end up having buyer's remorse about it. But after this thought experiment about remorse, I can see why some people would not have it even when they buy a really expensive Mac. If you're a Final Cut Pro guy, it's only way you can get your creative tool. So that makes sense.
BTW, when Bubble 2.0 pops, Apple is going down too: all of these dot coms that have been buying their people Apple equipment will stop. I know that Apple needs to be shorted, especially since their stock had a $12 pop after hours today. The problem is "when"? Usually the best time to short a stock is when I thought it was overhyped all along and then finally conclude it's time to buy. I'm not there yet, so hold on a while, shorties.